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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-04-09 21:16:35 UTC
Update Date2019-07-23 07:13:18 UTC
HMDB IDHMDB0059964
Secondary Accession Numbers
  • HMDB59964
Metabolite Identification
Common Name2,3,4-Trihydroxybenzoic acid
Description2,3,4-Trihydroxybenzoic acid belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. 2,3,4-Trihydroxybenzoic acid, along with other phenol compounds isolated from Pachysandra terminalis, showed significant antioxidant activity (PMID: 20939276 ). 2,3,4-Trihydroxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563865998
Synonyms
ValueSource
2,3,4-TrihydroxybenzoateGenerator
234-Trihydroxybenzoic acidHMDB
234-TrihydroxybenzoateHMDB
Chemical FormulaC7H6O5
Average Molecular Weight170.1195
Monoisotopic Molecular Weight170.021523302
IUPAC Name2,3,4-trihydroxybenzoic acid
Traditional Name2,3,4-trihydroxybenzoic acid
CAS Registry Number610-02-6
SMILES
OC(=O)C1=C(O)C(O)=C(O)C=C1
InChI Identifier
InChI=1S/C7H6O5/c8-4-2-1-3(7(11)12)5(9)6(4)10/h1-2,8-10H,(H,11,12)
InChI KeyBRRSNXCXLSVPFC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylic acids
Alternative Parents
Substituents
  • Salicylic acid
  • 5-unsubstituted pyrrogallol
  • Benzenetriol
  • Benzoic acid
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.41 g/LALOGPS
logP10(1.19) g/LALOGPS
logP10(1.37) g/LChemAxon
logS10(-1.5) g/LALOGPS
pKa (Strongest Acidic)2.88ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.26 m³·mol⁻¹ChemAxon
Polarizability14.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.97731661259
DarkChem[M-H]-130.78231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3,4-Trihydroxybenzoic acidOC(=O)C1=C(O)C(O)=C(O)C=C12948.4Standard polar33892256
2,3,4-Trihydroxybenzoic acidOC(=O)C1=C(O)C(O)=C(O)C=C11666.3Standard non polar33892256
2,3,4-Trihydroxybenzoic acidOC(=O)C1=C(O)C(O)=C(O)C=C11478.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,3,4-Trihydroxybenzoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O)C(O)=C1O1954.8Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,1TMS,isomer #2C[Si](C)(C)OC1=C(C(=O)O)C=CC(O)=C1O1853.4Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,1TMS,isomer #3C[Si](C)(C)OC1=C(O)C=CC(C(=O)O)=C1O1865.3Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,1TMS,isomer #4C[Si](C)(C)OC1=CC=C(C(=O)O)C(O)=C1O1914.8Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C(O)=C1O1867.9Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=C(O)C(O[Si](C)(C)C)=C1O1833.5Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC=C(O)C(O)=C1O[Si](C)(C)C1856.3Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(C(=O)O)C(O[Si](C)(C)C)=C1O1885.6Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TMS,isomer #5C[Si](C)(C)OC1=C(O)C=CC(C(=O)O)=C1O[Si](C)(C)C1858.6Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TMS,isomer #6C[Si](C)(C)OC1=CC=C(C(=O)O)C(O)=C1O[Si](C)(C)C1867.9Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1O1915.0Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C(O)=C1O[Si](C)(C)C1920.9Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC=C(O)C(O[Si](C)(C)C)=C1O[Si](C)(C)C1904.9Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,3TMS,isomer #4C[Si](C)(C)OC1=CC=C(C(=O)O)C(O[Si](C)(C)C)=C1O[Si](C)(C)C1891.5Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1O[Si](C)(C)C1959.3Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O)C(O)=C1O2231.2Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(C(=O)O)C=CC(O)=C1O2181.4Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C=CC(C(=O)O)=C1O2160.3Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)O)C(O)=C1O2234.5Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1O2387.2Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1O2338.7Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O)C(O)=C1O[Si](C)(C)C(C)(C)C2358.0Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=C1O2440.9Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=C(O)C=CC(C(=O)O)=C1O[Si](C)(C)C(C)(C)C2386.7Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)O)C(O)=C1O[Si](C)(C)C(C)(C)C2409.8Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1O2591.6Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1O[Si](C)(C)C(C)(C)C2596.0Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2585.0Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2654.6Semi standard non polar33892256
2,3,4-Trihydroxybenzoic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2796.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,4-Trihydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmi-1900000000-b9b7e315698e097f52392017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,4-Trihydroxybenzoic acid GC-MS (4 TMS) - 70eV, Positivesplash10-00dl-3019300000-57bb9bd14298886481bc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,4-Trihydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 10V, Positive-QTOFsplash10-0udi-0900000000-c2d0a9f1b869b3119d622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 20V, Positive-QTOFsplash10-0ufr-4900000000-36a3bab8198b0169443e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 10V, Negative-QTOFsplash10-0udi-0900000000-192a815c13b8c99897902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 40V, Positive-QTOFsplash10-0udi-9000000000-8319007060132bdc607e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 40V, Negative-QTOFsplash10-0uxu-9100000000-778e0f213c7da88e6ee32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 20V, Negative-QTOFsplash10-0zor-4900000000-90af5a82e82fdd1b96802021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 10V, Positive-QTOFsplash10-0fk9-0900000000-b12056f17b6aa0e4746f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 20V, Positive-QTOFsplash10-0ufr-0900000000-327e96bbbf6370563da22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 40V, Positive-QTOFsplash10-00kb-9400000000-f7d9e0d8e57f952f37a12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 10V, Negative-QTOFsplash10-016r-0900000000-abdc4b141346cc0a0ff12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 20V, Negative-QTOFsplash10-004i-0900000000-0cf40fa83622d0534fb82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4-Trihydroxybenzoic acid 40V, Negative-QTOFsplash10-05r0-9600000000-532246bba16bb3a933372017-10-06Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.001 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11874
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. J Nutr. 2009 Dec;139(12):2309-14. doi: 10.3945/jn.109.113613. Epub 2009 Oct 7. [PubMed:19812218 ]
  2. Zhai H, Li C, Tang S, Duan H: [Phenol constituents of Pachysandra terminalis and their antioxidant activity]. Zhongguo Zhong Yao Za Zhi. 2010 Jul;35(14):1820-3. [PubMed:20939276 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2,3,4-Trihydroxybenzoic acid → 6-(6-carboxy-2,3-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2,3,4-Trihydroxybenzoic acid → 6-(4-carboxy-2,3-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2,3,4-Trihydroxybenzoic acid → 6-(3-carboxy-2,6-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2,3,4-Trihydroxybenzoic acid → 3,4,5-trihydroxy-6-(2,3,4-trihydroxybenzoyloxy)oxane-2-carboxylic aciddetails
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
2,3,4-Trihydroxybenzoic acid → 2-{[hydroxy(2,3,4-trihydroxyphenyl)methylidene]amino}acetic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
2,3,4-Trihydroxybenzoic acid → 2,4-dihydroxy-3-(sulfooxy)benzoic aciddetails